2-Bromo-3-hydroxypyridine supplier

Name
2-Bromo-3-hydroxypyridine
EINECS 229-547-5
CAS No. 6602-32-0
Article Data20
CAS DataBase
Density 1.788 g/cm³
Solubility Soluble in alcohol. Insoluble in water.
Melting Point 185-188 °C(lit.)
Formula C₅H₄BrNO
Boiling Point 321.7 °C at 760 mmHg
Molecular Weight 173.997
Flash Point 148.4 °C
Transport Information
Appearance Light brown to grey crystalline powder
Safety 26-36-24/25
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 3-Pyridinol, 2-bromo-;2-Bromo-3-pyridinol;2-Bromopyridin-3-ol;3-Hydroxy-2-bromopyridine;
PSA 33.12000
LogP 1.54970

Synthetic route

: 24100-18-3
2-bromo-3-methoxypyridine

: 6602-32-0
2-bromo-pyridin-3-ol

Conditions

Conditions	Yield
With hydrogen bromide In dichloromethane at 140℃; Inert atmosphere;	94%

: 109-00-2
3-HYDROXYPYRIDINE

: 6602-32-0
2-bromo-pyridin-3-ol

Conditions

Conditions	Yield
With bromine; sodium hydroxide In water at -10 - 20℃; for 3h;	75%
With bromine; sodium hydroxide In water at -10 - 20℃; for 3h; Temperature;	75%
With bromine; acetic acid In sodium hydroxide	67%

: 109-00-2
3-HYDROXYPYRIDINE

A: 6602-32-0
2-bromo-pyridin-3-ol

B: 6602-33-1
2,6-dibromopyridin-3-ol

C: 129611-31-0
2,4-Dibromo-3-hydroxypyridine

Conditions

Conditions	Yield
With sodium hydroxide; bromine In water for 3h;	A 68% B n/a C n/a
With bromine; sodium hydroxide In water for 24h; Cooling with ice;	A 16% B 18% C 7%
With sodium hydroxide; bromine In water for 3h; Product distribution; other reaction conditions;

...Expand

: methanesulfonic acid 2-bromopyridin-3-yl ester

: 6602-32-0
2-bromo-pyridin-3-ol

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at 23℃; for 0.5h;	57%

: 109-00-2
3-HYDROXYPYRIDINE

A: 6602-32-0
2-bromo-pyridin-3-ol

B: 6602-33-1
2,6-dibromopyridin-3-ol

Conditions

Conditions	Yield
With bromine In sodium hydroxide; water; ethyl acetate	A n/a B 29%
Stage #1: 3-HYDROXYPYRIDINE With bromine; sodium hydroxide In water at 0℃; for 1.5h; Stage #2: With hydrogenchloride In water pH=2; Stage #3: In hexane; ethyl acetate for 72h;	A n/a B 20%

: 15128-82-2
3-hydroxy-2-nitropyridine

: 6602-32-0
2-bromo-pyridin-3-ol

Conditions

Conditions	Yield
With phosphorus tribromide

: 74037-50-6
3-ethoxy-2-nitropyridine

: 6602-32-0
2-bromo-pyridin-3-ol

Conditions

Conditions	Yield
With water; hydrogen bromide; acetic acid at 130℃; unter Druck;

: 38729-14-5
2-nitro-1-oxy-pyridin-3-ol

: 6602-32-0
2-bromo-pyridin-3-ol

Conditions

Conditions	Yield
With chloroform; phosphorus tribromide

: 110-86-1
pyridine

: 109-00-2
3-HYDROXYPYRIDINE

: 7726-95-6
bromine

: 6602-32-0
2-bromo-pyridin-3-ol

...Expand

: 109-00-2
3-HYDROXYPYRIDINE

A: 6602-32-0
2-bromo-pyridin-3-ol

B: 6602-33-1
2,6-dibromopyridin-3-ol

C: 6602-34-2
2,4,6-tribromo-3-hydroxypyridine

Conditions

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane at 20℃; for 48h;	A 28 % Spectr. B 32 % Spectr. C 4 % Spectr.

...Expand

: 626-55-1
3-Bromopyridine

: 6602-32-0
2-bromo-pyridin-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol / 165 °C 2: sulfuric acid; nitric acid 3: water; acetic acid; hydrobromic acid / 130 °C / unter Druck View Scheme

: 6602-28-4
3-hydroxypyridine N-oxide

: 6602-32-0
2-bromo-pyridin-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid 2: chloroform; phosphorus (III)-bromide View Scheme

: 14773-50-3
3-ethoxypyridine

: 6602-32-0
2-bromo-pyridin-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid 2: water; acetic acid; hydrobromic acid / 130 °C / unter Druck View Scheme

: 6602-32-0
2-bromo-pyridin-3-ol

: 108-24-7
acetic anhydride

: 92671-70-0
acetic acid 2-bromopyridin-3-yl ester

Conditions

Conditions	Yield
for 3h; Reflux;	100%
for 1h; Heating / reflux;	99%
at 150℃; for 5h;	95%

: 6602-32-0
2-bromo-pyridin-3-ol

: 113534-13-7
(2S)-1-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-2-propanol

: 1047664-32-3
C14H24BrNO2Si

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;	100%

: 75-30-9
2-iodo-propane

: 6602-32-0
2-bromo-pyridin-3-ol

: 113503-65-4
2-bromo-3-isopropoxypyridine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h;	99%
With sodium hydride 1.) DMF, 0 deg C, 10 min, 2.) DMF, 70 deg C, 3 h; Yield given. Multistep reaction;

: 6602-32-0
2-bromo-pyridin-3-ol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 870635-26-0
2-bromo-3-{[tert-butyl(dimethyl)silyl]oxy}pyridine

Conditions

Conditions	Yield
With triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 12h;	99%

: 6602-32-0
2-bromo-pyridin-3-ol

: 100-39-0
benzyl bromide

: 132330-98-4
3-benzyloxy-2-bromopyridine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h;	99%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 55℃; for 3h;
With potassium carbonate In N,N-dimethyl-formamide at 20 - 55℃; for 3h;

: 6602-32-0
2-bromo-pyridin-3-ol

: 4548-45-2
2-chloro-5-nitropyridine

: 1190847-06-3
C10H6BrN3O3

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 8h;	99%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 8h;	99%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 8h;	99%

: 6602-32-0
2-bromo-pyridin-3-ol

: 50-00-0
formaldehyd

: 2-bromo-6-(hydroxymethyl)pyridin-3-ol

Conditions

Conditions	Yield
With ethylenediaminetetraacetic acid disodium salt dihydrate; potassium hydroxide In water at 90℃; for 5h;	99%

: 6602-32-0
2-bromo-pyridin-3-ol

: 536-74-3
phenylacetylene

: 18068-82-1
2-phenylfuro<3,2-b>pyridine

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-pyridine-2,6-diamine; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 1h; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere;	99%
With 5%-palladium/activated carbon; caesium carbonate; lithium chloride In N,N-dimethyl-formamide at 150℃; for 16h; Reagent/catalyst; Temperature;	82%

: 6602-32-0
2-bromo-pyridin-3-ol

: 585-71-7, 38661-81-3
(1-bromoethyl)benzne

: (±)-2-bromo-3-(1-phenylethoxy)pyridine

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 60℃; for 18h;	99%

: 6602-32-0
2-bromo-pyridin-3-ol

: 620-13-3
1-bromomethyl-3-methyl-benzene

: 2-bromo-3-((3-methylbenzyl)oxy)pyridine

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 60℃; for 15.5h;	99%

: 6602-32-0
2-bromo-pyridin-3-ol

: 511286-63-8
(4S) 3,4-dibenzyl[1,2,3]oxathiazolidine-2,2-dioxide

: benzyl [(S)-1-(2-bromopyridin-3-yloxymethyl)-2-phenylethyl]amine

Conditions

Conditions	Yield
Stage #1: 2-bromo-pyridin-3-ol; (4S) 3,4-dibenzyl[1,2,3]oxathiazolidine-2,2-dioxide With sodium hydride In N,N-dimethyl-formamide at 20℃; for 16h; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide at 20℃; for 2h; Further stages.;	98%

: 6602-32-0
2-bromo-pyridin-3-ol

: 873-74-5
4-Aminobenzonitrile

: 4-((3-hydroxypyridin-2-yl)amino)benzonitrile

Conditions

Conditions	Yield
With [COD(Pd-AlPhos)2]; 1,8-diazabicyclo[5.4.0]undec-7-ene In tert-butyl methyl ether at 20℃; for 3h; Inert atmosphere; Sealed tube; Schlenk technique;	98%

: 6602-32-0
2-bromo-pyridin-3-ol

: 513-31-5
2-bromoallyl bromide

: 99029-94-4
2-bromo-3-(2'-bromoallyl)pyridinyl ether

Conditions

Conditions	Yield
With potassium carbonate In acetone Heating;	97%

: 6602-32-0
2-bromo-pyridin-3-ol

: 14301-31-6
2-chloro-N-(2-(3,4-dimethoxyphenyl)ethyl)acetamide

: 596808-09-2
2-(2-bromopyridin-3-yloxy)-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile Heating;	97%

: 6602-32-0
2-bromo-pyridin-3-ol

: 34164-16-4
N-[2-(3,4-dimethoxyphenyl)ethyl]-2-chloropropanamide

: 2-(2-bromopyridin-3-yloxy)-N-[2-(3,4-dimethoxyphenyl)ethyl]propionamide

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile Heating;	97%

: 6602-32-0
2-bromo-pyridin-3-ol

: 94318-76-0
2-chloro-propionic acid cyclohexylamide

: 596808-05-8
2-(2-bromopyridin-3-yloxy)-N-cyclohexylpropionamide

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile Heating;	97%

: 6602-32-0
2-bromo-pyridin-3-ol

: 124-63-0
methanesulfonyl chloride

: methanesulfonic acid 2-bromopyridin-3-yl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 18h;	97%
With potassium carbonate In acetone at 23℃; for 1h;	94%

: 6602-32-0
2-bromo-pyridin-3-ol

: 129611-32-1
2-bromo-6-iodopyridin-3-ol

Conditions

Conditions	Yield
With iodine; potassium carbonate In water at 15℃;	97%
With iodine; potassium carbonate In water at 20℃; for 72h; Product distribution / selectivity;	96%
With iodine; potassium carbonate In water at 20℃; for 5h;	96%

: 6602-32-0
2-bromo-pyridin-3-ol

: 23605-23-4
2-Chloro-N-cyclohexylacetamide

: 2-(2-bromopyridin-3-yloxy)-N-cyclohexylacetamide

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile Heating;	96%

: 763-32-6
2-methyl-1-buten-4-ol

: 6602-32-0
2-bromo-pyridin-3-ol

: 2-bromo-3-((3-methylbut-3-en-1-yl)oxy)pyridine

Conditions

Conditions	Yield
Stage #1: 2-methyl-1-buten-4-ol; 2-bromo-pyridin-3-ol With triphenylphosphine In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: With di-isopropyl azodicarboxylate; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	96%

: 6602-32-0
2-bromo-pyridin-3-ol

: 85118-00-9
2,6-Difluorobenzyl bromide

: 2-bromo-3-((2,6-difluorobenzyl)oxy)pyridine

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 60℃; for 15h;	96%

: 6602-32-0
2-bromo-pyridin-3-ol

: 37002-45-2
(4S,5S)-2,2-dimethyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolan

: 137129-41-0
(+)-(4S-trans)-<4,5-dimethanol-2,2-dimethyl-1,3-dioxolane>-bis<3-(2-bromo)pyridine>

Conditions

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In toluene at 85℃; for 48h;	95%

: 6602-32-0
2-bromo-pyridin-3-ol

: 2564-06-9
N-benzyl-2-chloroacetamide

: 596808-00-3
2-(2-bromopyridin-3-yloxy)-N-benzylacetamide

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile Heating;	95%

: 6602-32-0
2-bromo-pyridin-3-ol

: 13156-95-1
2-chloro-N-phenethylacetamide

: 596808-11-6
2-(2-bromopyridin-3-yloxy)-N-phenethylacetamide

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile Heating;	95%

: 6602-32-0
2-bromo-pyridin-3-ol

: 40914-11-2
2-chloro-N-(cyclohexylmethyl)acetamide

: 596808-06-9
2-(2-bromopyridin-3-yloxy)-N-cyclohexylmethylacetamide

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile Heating;	95%

: 6602-32-0
2-bromo-pyridin-3-ol

: 14267-92-6
1-chloro-4-pentyne

: 1161009-64-8
2-bromo-3-pent-4-yn-1-yloxypyridine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃;	95%

: 6602-32-0
2-bromo-pyridin-3-ol

: 2524-04-1
diethyl phosphorochloridothioate

: 83866-76-6
Thiophosphoric acid O-(2-bromo-pyridin-3-yl) ester O',O''-diethyl ester

Conditions

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran	95%

: 6602-32-0
2-bromo-pyridin-3-ol

: 627-19-0
1-Pentyne

: 17957-20-9
2-propylfuro[3,2-b]pyridine

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; caesium carbonate; lithium chloride In N,N-dimethyl-formamide at 150℃; for 18h;	95%

: 6602-32-0
2-bromo-pyridin-3-ol

: 358-23-6
trifluoromethylsulfonic anhydride

: 157373-97-2
2-bromo-3-pyridinyl trifluoromethanesulfonate

Conditions

Conditions	Yield
With pyridine at -10 - 23℃; for 1.75h;	94%
With triethylamine In dichloromethane at 0 - 20℃; Esterification;	93%
With triethylamine In diethyl ether at 0 - 20℃; for 12h; Inert atmosphere;	85%

: 6602-32-0
2-bromo-pyridin-3-ol

: 39089-62-8
2-chloro-N-[(tetrahydrofuran-2-yl)methyl]acetamide

: 596808-02-5
2-(2-bromopyridin-3-yloxy)-N-(tetrahydrofuran-2-ylmethyl)acetamide

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile Heating;	94%

2-Bromo-3-hydroxypyridine Specification

The 2-Bromo-3-hydroxypyridine, with the CAS registry number 6602-32-0, is also known as 2-Bromo-3-pyridinol. It belongs to the product categories of Blocks; Bromides; Pyridines; Pyridine; Pyridine Series; Pyridines, Pyrimidines, Purines and Pteredines; Pyridines derivatives; Halides; API intermediates; Bromopyridines; Halopyridines; Boronic Acid. Its EINECS number is 207-857-1. This chemical's molecular formula is C₅H₄BrNO and molecular weight is 174.00. What's more, its systematic name is 2-bromopyridin-3-ol. It should be sealed and stored in a cool and dry place. Moreover, it should be protected from light. It is used in organic synthesis.

Physical properties of 2-Bromo-3-hydroxypyridine are: (1)ACD/LogP: 1.66; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.64; (4)ACD/LogD (pH 7.4): 0.96; (5)ACD/BCF (pH 5.5): 10.25; (6)ACD/BCF (pH 7.4): 2.13; (7)ACD/KOC (pH 5.5): 181.48; (8)ACD/KOC (pH 7.4): 37.75; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 22.12 Å²; (13)Index of Refraction: 1.614; (14)Molar Refractivity: 33.91 cm³; (15)Molar Volume: 97.2 cm³; (16)Polarizability: 13.44×10^-24cm³; (17)Surface Tension: 56.7 dyne/cm; (18)Density: 1.788 g/cm³; (19)Flash Point: 148.4 °C; (20)Enthalpy of Vaporization: 58.6 kJ/mol; (21)Boiling Point: 321.7 °C at 760 mmHg; (22)Vapour Pressure: 0.000155 mmHg at 25°C.

Preparation: this chemical can be prepared by pyridin-3-ol at the temperature of 20 °C. This reaction will need reagents Br₂, HCl and solvent aq. NaOH. The yield is about 52%.

2-Bromo-3-hydroxypyridine can be prepared by pyridin-3-ol at the temperature of 20 °C

Uses of 2-Bromo-3-hydroxypyridine: it can be used to produce 2-bromo-3-isopropoxypyridine at the temperature of 80 °C. It will need reagent K₂CO₃ and solvent dimethylformamide with the reaction time of 2 hours. The yield is about 99%.

2-Bromo-3-hydroxypyridine can be used to produce 2-bromo-3-isopropoxypyridine at the temperature of 80 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing and must avoid contact with eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: Brc1ncccc1O
(2)Std. InChI: InChI=1S/C5H4BrNO/c6-5-4(8)2-1-3-7-5/h1-3,8H
(3)Std. InChIKey: YKHQFTANTNMYPP-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	320mg/kg (320mg/kg)		U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04679.

Product Name

2-Bromo-3-hydroxypyridine

Synthetic route

2-Bromo-3-hydroxypyridine Specification

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